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Bogdan A. Šolaja, Ph.D.

Innovation center, Studentski trg 12-16, Beograd
Department of Organic Chemistry

Phone:   011-2638606, 011-3336681 (lab), 011-3336659 (lab), 011-3336750 (office)

Phone (local):   681 (lab), 659 (lab), 750 (office)

Office:   433

Laboratory:   432, 468

E-mail:   bsolaja AT chem · bg · ac · rs

Personal data

Born 1951 Belgrade, married, three daughters.

Education and qualifications

1975: Undergraduate studies - Chemistry / Prirodno-matematički fakultet (Belgrade, Serbia)

1978: Master of science studies - Chemistry / Prirodno-matematički fakultet (Belgrade, Serbia)

1984: Doctoral academic (PhD) studies - Chemistry / Prirodno-matematički fakultet (Belgrade, Serbia)

History of employment

1976: Graduate associate / Prirodno-matematički fakultet (Belgrade, Serbia)

1978: Graduate assistant / Prirodno-matematički fakultet (Belgrade, Serbia)

1981: Assistant / Prirodno-matematički fakultet (Belgrade, Serbia)

1994: Assistant professor / University of Belgrade - Faculty of Chemistry (Belgrade, Serbia)

1995: Associate professor / University of Belgrade - Faculty of Chemistry (Belgrade, Serbia)

2001-2016: Full professor / University of Belgrade - Faculty of Chemistry (Belgrade, Serbia)

2016: Innovation center of the Faculty of Chemisty in Belgrade (Belgrade, Serbia)

Scientific interest

Organic chemistry: synthesis, investigation on the mechanisms and new reactions, synthetic applications of organoaluminium compounds.

Medicinal chemistry: tetraoxacyclohexanes – antimalarial and antitumour activity; chloroaminoquinolines - antimalarial activity and inhibition of botulinum toxins; steroidal quinones and their derivatives-antitumour activity.

Awards and merits

1993: Meritorious member of the Serbian Chemical Society

December 8, 2009: Honorary member of the Serbian Chemical Society

December 3, 2015: Medal for lasting and outstanding contribution to sciences
as an expression of recognition for the contribution the development of antimalarials and inhibitors of botulinum neurotoxin and Ebola

Other activities

Corresponding member of Serbian Academy of Sciences and Arts from November 2, 2006 to October 31, 2012 - Department of chemical and biological sciences.

Full member of Serbian Academy of Sciences and Arts from November 1, 2012 - Department of chemical and biological sciences.

Member of Serbian Chemical Society from 1975. Secretary of SCS from 1996 to 2001; vicepresident from 2001 to 2005; president from 2005 to 2009.

Member of Swiss Chemical Society from 1986.

Member of American Chemical Society from 1987 - Organic section; Section for medicinal chemistry..

Chief of the Department of Organic Chemistry from October 1, 2015.

Orcid.org/0000-0002-9975-2725

Projects

Project leader:

Project researcher:

Representative references

Knjige i revijalni radovi / Books and reviews:

  1. Preveo i uredio udžbenik Organska hemija (Organic chemistry), 2. i 4. američko izdanje (1994, 2003) autora K.P.C. Vollhardt-a i N. Shore-a, W.H. Freeman and Company, Datastatus Beograd. Prevod priručnika Uputstvo za rešavanje zadataka sa rešenjima. Organska hemija, struktura i funkcija. (The Study Guide) N. Schore, W.H. Freeman and Company

Reviews

  1. Reactions and Use of Diisobutylaluminium Hydride in Organic Synthesis, J. Serb. Chem. Soc., 1993, 58, 155-191, and the references cited therein.
  2. Antimalarial peroxides. Dejan M. Opsenica, Bogdan A. Šolaja. Journal of the Serbian Chemical Society 2009, 74, 1155–1193.
  3. Dejan M. Opsenica, Bogdan A. Šolaja, “Second-Generation Peroxides: The OZs and Artemisone” in “Treatment and Prevention of Malaria: Antimalarial Drug Chemistry, Action and Use”, Henry M. Staines, Sanjeev Krishna, (Eds.); Series: Milestones in Drug Therapy; Series Editors: Michael J. Parnham, Jacques Bruinvels. Springer, Basel, 2012. ISBN 978-3-0346-0479-6
  4. Artemisinins and synthetic peroxides as highly efficient antimalarials. Dejan M. Opsenica, Bogdan A. Šolaja. Macedonian Journal of Chemistry and Chemical Engineering, 2012, 31, 137–182.

Izabrani radovi / Selected papers:

Antimalarials

  1. Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: structure determination and their antimalarial activity, N. Todorović, M. Stefanović, B. Tinant, J-P. Declercq, M. Makler, B. Šolaja, Steroids, 1996, 61, 688-696.
  2. Cholic Acid Derivatives as 1,2,4,5-Tetraoxane Carriers: Structure, Antimalarial and Antiproliferative Activity. D. Opsenica, G. Pocsfalvi, Z. Juranić, B Tinant, J.-P. Declercq, D. E. Kyle, W. K. Milhous, B. A. Šolaja, J. Med. Chem., 2000,43, 3274-3282.
  3. Mixed Steroidal 1,2,4,5-Tetraoxanes: Antimalarial and Antimycobacterial Activity. B. A. Šolaja, N. Terzić, G. Pocsfalvi, L. Gerena, B. Tinant, D. Opsenica, W. K. Milhous, J. Med. Chem., 2002, 45, 3331-3336.
  4. Antimalarial, antimycobacterial and antiproliferative activity of phenyl substituted mixed tetraoxanes. D. Opsenica, D. E. Kyle, W. K. Milhous, B. A. Šolaja, J. Serb. Chem. Soc., 2003, 68, 291–302.
  5. Antimalarial and Antiproliferative Evaluation of Bis-Steroidal Tetraoxanes. D. Opsenica, G. Angelovski, G. Pocsfalvi, Z. Juranić, Ž. Žižak, D. Kyle, W. K. Milhous, B. A. Šolaja, Bioorganic & Medicinal Chemistry, 2003, 11, 2761-2768.
  6. Structure-activity relationship study of steroidal 1,2,4,5-tetraoxane antimalarials using computational procedures. A. K. Bhattacharjee, K. A. Carvalho, D. Opsenica, B. A. Šolaja, J. Serb. Chem. Soc., 2005, 70, 329-345.
  7. Tetraoxane Antimalarials and Their Reaction with Fe(II). I. Opsenica, N. Terzić, D. Opsenica, G. Angelovski, M. Lehnig, P. Eilbracht, B. Tinant, Z. Juranić, K. S. Smith, Y. S. Yang, D. S. Diaz, P. L. Smith, W. K. Milhous, D. Doković, B. A. Šolaja, J. Med. Chem., 2006, 49, 3790-3799.
  8. Deoxycholic Acid-Derived Tetraoxane Antimalarials and Antiproliferatives. N. Terzić, D. Opsenica, D. Milić, B. T., K. S. Smith, W. K. Milhous, B. A. Šolaja, J. Med. Chem., 2007, 50, 5118-5127.
  9. On peroxide antimalarials. I. Opsenica, D. Opsenica, M. Jadranin, K. S. Smith, W. K. Milhous, M. Stratakis and B. Šolaja. J. Serb. Chem. Soc., 2007, 71, 1181–1190.
  10. Chemical Stability of the Peroxide Bond Enables Diversified Synthesis of Potent Tetraoxane Antimalarials. Opsenica, I.; Opsenica, D.; Smith, K.S.; Milhous, W.K.; Šolaja, B.A. J. Med. Chem., 2008, 51, 2261-2266.
  11. Mixed tetraoxanes containing the acetone subunit as antimalarials. Dejan M. Opsenica, Nataša Terzić, Philip L. Smith, Youngsun Yang, Lalaine Anova, Kirsten S. Smith, Bogdan A. Šolaja. Bioorganic & Medicinal Chemistry, 2008, 16, 7039–7045.
  12. New Chimeric Antimalarials with 4-Aminoquinoline Moiety Linked to a Tetraoxane Skeleton. Opsenica, Igor; Opsenica, Dejan; Lanteri, Charlotte Anne; Anova, Lalaine; Milhous, Wilbur K.; Smith, Kirsten S.; Šolaja, Bogdan A. J. Med. Chem., 2008, 51, 6216-6219.
  13. Mixed steroidal tetraoxanes induce apoptotic cell death in tumor cells. Žižak, Ž.; Juranić, Z.; Opsenica, D.; Šolaja, B. Investigational New Drugs, 2009, 27, 432-439.
  14. Correlation between structure, retention and activity of cholic acid derived cis–trans isomeric bis-steroidal tetraoxanes. Šegan, S., Andrić, F., Radoičić, A., Opsenica, D., Šolaja, B., Zlatović, M. and Milojković-Opsenica, D. J. Sep. Sci. 2011, 34, 1–9.
  15. 4-Amino-7-chloroquinolines: Probing ligand efficiency provides botulinum neurotoxin serotype a light chain inhibitors with significant antiprotozoal activity. Opsenica, I.M., Tot, M., Gomba, L., Nuss, J.E. , Sciotti, R.J., Bavari, S., Burnett, J.C., Šolaja, B.A. Journal of Medicinal Chemistry, 2013, 56 (14), 5860-5871.
  16. Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria. Videnović M, Opsenica DM, Burnett JC, Gomba L, Nuss JE, Selaković Z, Konstantinović J, Krstić M, Segan S, Zlatović M, Sciotti RJ, Bavari S, Solaja BA. J Med Chem. 2014, 57, 4134-4153.
  17. Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. Sandra Šegan, Nataša Terzić-Jovanović, Dušanka Milojković-Opsenica, Jelena Trifković, Bogdan Šolaja, Dejan Opsenica. Journal of Pharmaceutical and Biomedical Analysis 2014, 97, 178-183.
  18. I. M. Opsenica, T. Ž. Verbić, M. Tot, R. J. Sciotti, B. S. Pybus, O. Djurković-Djaković, K. Slavić, B. A. Šolaja, Investigation into novel thiophene- and furan-based 4-amino-7-chloroquinolines afforded antimalarials that cure mice, Bioorg. Med. Chem. 2015, 23, 2176-2186.
  19. Re-investigating old pharmacophores: Are 4-aminoquinolines and tetraoxanes potential two-stage antimalarials? Natasa Terzić, Jelena Konstantinović, Mikloš Tot, Jovana Burojević, Olgica Djurković-Djaković,  Jelena Srbljanović,Tijana Štajner,Tatjana Verbić, Mario Zlatović, Marta Machado, Inês S. Albuquerque, Miguel Prudêncio, Rick Sciotti,Stevan Pecic,Sarah D’Alessandro, Donatella Taramelli, Bogdan A. Šolaja. J. Med. Chem. Just Accepted Manuscript , DOI: 10.1021/acs.jmedchem.5b01374.

Botulinum Neurotoxin Inhibitors

  1. A Refined Pharmacophore Identifies Potent 4-Amino-7-chloroquinoline-Based Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease. J. C. Burnett, D. Opsenica, K. Sriraghavan, R. G. Panchal, G. Ruthel, A. R. Hermone, T. L. Nguyen, T. A. Kenny, D. J. Lane, C. F. McGrath, J. J. Schmidt, J. L. Vennerstrom, R. Gussio, B. A. Šolaja, S. Bavari. J. Med. Chem., 2007, 50, 2127-2136.
  2. Novel 4-Aminoquinolines Active against Chloroquine-Resistant and Sensitive P. falciparum Strains that also Inhibit Botulinum Serotype A. Bogdan A. Šolaja, Dejan Opsenica, Kirsten S. Smith, Wilbur K. Milhous, Nataša Terzić, Igor Opsenica, James C. Burnett, Jon Nuss, Rick Gussio, Sina Bavari. J. Med. Chem., 2008, 51, 4388–4391.
  3. Three-Dimensional Database Mining Identifies a Unique Chemotype that Unites Structurally Diverse Botulinum Neurotoxin Serotype A Inhibitors in a Three-Zone Pharmacophore. Hermone, A.R.; Burnett, J. C.; Nuss, J. E.; Tressler, L. E.; Nguyen, T. L.;Šolaja, B.A., Vennerstrom, J. V.; Schmidt, J. J.; Wipf, P.; Bavari, S.; Gussio, R. ChemMedChem, 2008, 3, 1905-1912.
  4. A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus. Igor Opsenica, James C. Burnett, Rick Gussio, Dejan Opsenica, Nina Todorović, Charlotte A. Lanteri, Richard J. Sciotti, Montip Gettayacamin, Nicoletta Basilico, Donatella Taramelli, Jonathan E. Nuss, Laura Wanner, Rekha G. Panchal, Bogdan A. Šolaja, Sina Bavari. Journal of Medicinal Chemistry  201154,  1157–1169.
  5. The synthesis of 2,5-Bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease. Igor Opsenica, Vuk Filipovic, Jon E. Nuss, Laura M. Gomba, Dejan Opsenica, James C. Burnett, Rick Gussio, Sina Bavari, Bogdan A. Solaja. European Journal of Medicinal Chemistry, 2012, 53, 374-379.
  6. 4-Amino-7-chloroquinolines: Probing ligand efficiency provides botulinum neurotoxin serotype a light chain inhibitors with significant antiprotozoal activity. Opsenica, I.M., Tot, M., Gomba, L., Nuss, J.E. , Sciotti, R.J., Bavari, S., Burnett, J.C., Šolaja, B.A. Journal of Medicinal Chemistry, 2013, 56 (14), 5860-5871.
  7. New 9-aminoacridine derivatives as inhibitors of botulinum neurotoxins and P. falciparum malaria. Mikloš Tot, Dejan M. Opsenica, Milena Mitrić, James C. Burnett, Laura Gomba, Sina Bavari, Bogdan A. Šolaja. J. Serb. Chem. Soc. 2013, 78 (12), 1847–1864.
  8. Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria. Videnović M, Opsenica DM, Burnett JC, Gomba L, Nuss JE, Selaković Z, Konstantinović J, Krstić M, Segan S, Zlatović M, Sciotti RJ, Bavari S, Solaja BA. J Med Chem. 2014, 57, 4134-4153.

Ebola inhibitors

  1. A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus. Igor Opsenica, James C. Burnett, Rick Gussio, Dejan Opsenica, Nina Todorović, Charlotte A. Lanteri, Richard J. Sciotti, Montip Gettayacamin, Nicoletta Basilico, Donatella Taramelli, Jonathan E. Nuss, Laura Wanner, Rekha G. Panchal, Bogdan A. Šolaja, Sina Bavari. J. Med. Chem. 201154, 1157–1169.
  2. A Limited Structural Modification Results in a Significantly More Efficacious Diazachrysene-Based Filovirus Inhibitor. Života Selaković, Dejan Opsenica, Brett Eaton, Cary Retterer, Sina Bavari, James C. Burnett, Bogdan A. Šolaja, Rekha G. Panchal. Viruses 2012, 4, 1279-1288.
  3. Anti-Ebola Activity of Diazachrysene Small Molecules. Života Selaković, Veronica Soloveva, Dima N. Gharaibeh, Jay Wells, Sandra Šegan, Rekha G. Panchal, and Bogdan A. Šolaja. ACS Infect. Dis. 2015, 1, 264−271.

Miscellaneous

  1. Steroidal Analogue of Deoxyvernolepin. Synthesis of gamma-Lactone Key Intermediate, B. Šolaja, M. Stefanović, Croat. Chim. Acta, 1986, 59, 1.
  2. The Synthesis of Trimethylcyclopentanecarboxylic Acids, B. Šolaja, J. Huguet, M. Karpf, A.S. Dreiding, Helv. Chim. Acta, 1986, 69, 1163.
  3. The Synthesis of (+,-)-Isoptychanolide by Application of the alpha-Alkynone Cyclisation, B. Šolaja, J. Huguet, M. Karpf, A.S. Dreiding, Tetrahedron, 1987, 43, 4875.
  4. Transformations of Some Steroidal Lactones and Study of Nucleophilic Substitution at 6alpha,7beta-Epoxides, B. Šolaja, Lj. Došen-Mićović, J. Serb. Chem. Soc., 1989, 54, 657.
  5. Oxidation of steroidal 5-en-3beta-ols with Jones reagent in ether, B. Šolaja, D. Milić, Lj. Došen-Mićović, Steroids, 1994, 59, 330-334.
  6. A Novel m-CPBA Oxidation: p-Quinols and Epoxyquinols from Phenols, B. Šolaja, D. Milić, M. Gašić, Tetrahedron Lett., 1996 (21) 3765-3768.
  7. The Synthesis and Biological Evaluation of A-Ring Substituted Steroidal p-Quinones, D. Milić, M. Gašić, W. Muster, J. Csanadi, B. Šolaja, Tetrahedron, 1997, 53, 14073-14084.
  8. The synthesis and in vitro activity of some DELTA7,9(11)-lanostadienes, B. Šolaja, M. Đermanović, D-M. Lim, Y-K. Paik, B. Tinant, J-P. Declerq, Steroids, 1997, 62, 709-718.
  9. Synthesis and Antiproliferative Activity of Epoxy and Bromo Compounds Derived from Estrone. D. R. Milić, T. Kop, Z. Juranić, M. J. Gašić, B. A. Šolaja, Bioorganic and Medicinal Chemistry Letters, 2001, 11, 2197-2200.
  10. Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds. D. Milić, T. Kop, Z. Juranić, M. J. Gašić, B. Tinant, G. Pocsfalvi, B. A. Šolaja, Steroids, 2005, 70, 922-932.
  11. Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system. Dragana Milica, Tatjana Kop, Janos Csanadi, Zorica Juranic, Zeljko Zizak, Miroslav J. Gasic, Bogdan Solaja. Steroids, 2009, 74, 890–895.
  12. Double Palladium-Catalyzed Synthesis of Azepines. Nina Božinović, Igor Opsenica, Bogdan A. Šolaja, Synlett 2013, 24 (1), 49.
  13. Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives. Šegan, S, Trifković, J. Verbić, T., Opsenica, D., Zlatović, M., Burnett, J., Šolaja, B., Milojković-Opsenica, D. Journal of Pharmaceutical and Biomedical Analysis  2013, 72, 231-239.

Patents

  1. YU-49004/03. Lanosta-7,9-dien-3alpha,32-diol i postupak za njegovu sintezu.
  2. US 6,906,098 B2. Mixed Steroidal 1,2,4,5-Tetraoxane Compounds and Methods of Making and Using Thereof.
  3. YU-49498. Katalitički postupak za dobivanje hidrazida nikotinskih kiselina.
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